Asymmetric Epoxidation Using Iminium Salt Organocatalysts Featuring Dynamically Controlled Atropoisomerism

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• 作者：Philip C. Bulman Page ; Christopher J. Bartlett ; Yohan Chan ; David Day ; Phillip Parker ; Benjamin R. Buckley ; Geracimos A. Rassias ; Alexandra M. Z. Slawin ; Steven M. Allin ; J茅r么me Lacour ; Andr茅 Pinto
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：July 20, 2012
• 年：2012
• 卷：77
• 期：14
• 页码：6128-6138
• 全文大小：563K
• 年卷期：v.77,no.14(July 20, 2012)
• ISSN：1520-6904

文摘

Introduction of a pseudoaxial substituent at a stereogenic center adjacent to the nitrogen atom in binaphthyl- and biphenyl-derived azepinium salt organocatalysts affords improved enantioselectivities and yields in the epoxidation of unfunctionalized alkenes. In the biphenyl-derived catalysts, the atropoisomerism at the biphenyl axis is controlled by the interaction of this substituent with the chiral substituent at nitrogen.